The proposed work would enable the convergent, enantioselective, and biomimetic synthesis of the alkaloid natural product (-)-communesin F. (-)-Communesin F belongs to a family of natural products containing a structurally unique heptacyclic framework. This family of natural products displays a range of interesting biological activities. A biosynthetically inspired rearrangement of a complex heterodimer should afford the core of the communesin alkaloids. Application of our newly developed method for heterodimerization will allow rapid access to the necessary dimer. The method centers on the stepwise union of complex amines in the form of unsymmetrical diazenes followed by photoexpulsion of dinitrogen to afford the heterodimerized product. In all, the proposed route will afford a rapid and convergent synthesis of (-)- communesin F which potentially could be expanded to all members of the communesin family of natural products. PUBLIC HEALTH RELEVANCE: Biologically active natural products continue to be utilized in a number of medicinal treatments. The efficient synthesis of these natural products allows not only for their testing against various diseases but also allows for the synthesis of potentially more potent derivatives. Here in we describe the purposed enantioselective synthesis of communesin F a member of a family of alkaloid natural products with varying biological activity. The proposed route will take advantage of the newly developed method for heterodimerization via diazene fragmentation as well as a biosynthetically inspired rearrangement to afford the communesin core.